Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

Day 2 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in Milan by discovering the best things there are to see and do in the city.

Make sure to visit Navigli, a popular neighborhood in Milan. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Milan. Begin your sightseeing with Duomo Di Milano Museum. This iconic church is one of the top attractions in the city. Proceed to Galleria Vittorio Emanuele Ii, another must-visit attraction.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Sforzesco Castle Art Library. This famous castle is a traveler-favorite. Not far away, you’ll find Parco Sempione, another key site on your sightseeing itinerary. Piazza Gae Aulenti is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a wonderful meal at Dessert Bar Milano, a top-rated dining spot in Milan. If you're in the mood for something new, try Radisson Blu Hotel Milan, another premier location with a delectable menu. You might also want to book a table at Ristorante Qui Si Mangia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

If you’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Como, Rogaro, Lenno, and Colonno, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Como. You’ll stay here for 1 night.

Immerse yourself in Milan’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Di San Fedele. This photogenic church is sure to ignite your curiosity. Next, dive into the enchanting features of Saint Mary Assunta Cathedral, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Villa Carlotta (lake Como), a beloved museum. We also recommend visiting Greenway Del Lago Di Como. This hiking area is a must for anyone looking to experience the city to the fullest.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Como. Como offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Como. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Make sure to reserve a table at L’Antica Trattoria, an iconic dining spot in Como. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Gesumin Restaurant, a popular restaurant in Como. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Pronobis, a hidden gem nestled in Como. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Fresco Cocktail Shop, a top-rated bar in the area. For other recommendations, Bar Il Cortiletto provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Pinocchio offers a memorable night with diverse drink options and excellent service.

Take some time to reflect on your day and savor another beautiful night in Italy.

On day 4 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Verona. In the evening, you’ll end up in Verona, where you will stay for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Como allows for both. Start by heading to Giusti Garden. This frequently visited botanical garden provides an insightful glimpse into the city's identity. Next, discover Ponte Pietra, a visually striking historical landmark, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Dei Signori, a curiosity-inducing public square. When you’re done, don’t forget to make a stop at the popular Piazza Delle Erbe. Not far away from the public square, you will find the visually striking Verona Arena, perfect for a quick visit. Round off your day at Castelvecchio Museum, another gem in Como with picture-perfect features to discover.

At the end of the day, you will drive to Verona, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat in Verona. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Savor the flavors at La Griglia, a top pick for dinner tonight. Alternatively, Vecio Macello beckons with its unique menu offerings. Also, consider Via Fama Cafè | Verona. With its consistent customer satisfaction, it’s an excellent option for dining in Verona tonight.

Cap off your dinner by heading to Archivio, ideal for a leisurely evening with a drink in hand. La Segreteria Café is another bar that offers an enjoyable setting. Similarly, Grande Giove Cocktail Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

Celebrate another amazing day of your road trip adventure in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Venice. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 2 nights.

Get ready to discover some of the most iconic wonders in Verona, including a church, an art gallery, and a street. Start your day at Santa Maria Della Salute. This romantic church is a locally appreciated place to see in Verona. Then, wander over to Peggy Guggenheim Collection. If enchanting sites excite you, this art gallery will be right up your alley. Nearby, you’ll also find Santa Maria Gloriosa Dei Frari. This culturally significant church is a favorite among visitors.

Verona offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Grand Canal is a locally appreciated spot in the city that will captivate you with its unique charm.

When you’re done exploring for the day, you’ll drive to your hotel in Venice. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Venice, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Treat yourself to a delightful dinner at Bauer Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try L'Osteria Le Guglie? It's another excellent option with a diverse menu. Consider reserving a table at Corner Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

After enjoying a fulfilling meal, continue your evening at Al Parlamento, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Caffe Rosso offers a welcoming atmosphere for easing into the nightlife. Similarly, Adagio provides an excellent environment for a relaxed and enjoyable evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Day 6 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Brace yourself for today’s incredible lineup of attractions in Venice, featuring fun adventures, romantic experiences, and scenic views. Start at Rialto Bridge, a globally renowned historical landmark in the city. Then, head to Teatro La Fenice and soak in the ambiance of this historic opera house.

There are many interesting places to see in Venice, and when you are ready for more, go to Piazza San Marco. This is one of the city’s most globally renowned enchanting spots of interest. After exploring the public square, visit the captivating St Mark's Basilica. Not far away, you'll also find Doge's Palace. This palace is a history-steeped highlight in Venice. Before wrapping up your self-guided sightseeing tour, head to Bridge Of Sighs, a captivating monument in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Venice's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at Generator Venice, a top recommendation for dinner tonight. Or, for a change of pace, Nevodi boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Piazza. Known as a local hotspot, it’s a great choice for tonight in Venice.

Cap off your dinner by heading to Il Mercante, ideal for a leisurely evening with a drink in hand. The Irish Pub Venezia is another bar that offers an enjoyable setting. Similarly, Ai Stagneri is also a popular place to go on a night out, perfect for relaxing and socializing.

Take some time to reflect on your day and savor another beautiful night in Italy.

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 3 nights.

Today's adventure in Venice promises more breathtaking discoveries and enriching experiences! Begin at Piazzale Michelangelo. This visually striking observation deck is a highlight of any visit in the city. Then, enjoy Basilica Of Santa Croce In Florence, another culturally significant attraction that never fails to captivate visitors.

If you’re looking for more, spend time soaking in the atmosphere of Central Market. This photogenic food market is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Cathedral Of Santa Maria Del Fiore, an astonishing church, and take a stroll around the area.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Say good night to Florence and look forward to another great day of your road trip in Italy!

Day 8 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

One of the most iconic places you can visit today in Florence is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Ponte Vecchio. This enchanting historical landmark is a highlight of any visit in the city. Then, enjoy Piazza Della Signoria, another majestic attraction that never fails to captivate visitors. Next, head over to Bargello National Museum, one of the city’s most increasingly popular attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Palazzo Vecchio. This visually striking palace is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Uffizi Gallery, an astonishing art gallery, and take a stroll around the area.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Wake up to day 9 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Santa Maria Della Spina. This increasingly popular church is one of the top attractions in the city. Proceed to Knights' Square, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Leaning Tower Of Pisa. This world-famous monument is a traveler-favorite. Not far away, you’ll find Pisa Cathedral, another key site on your sightseeing itinerary. Piazza Del Duomo, Pisa is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Campo Santo and uncover why it's recognized as one of the city's most intriguing attractions.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and recharge in preparation for another adventurous day in Italy!

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Savor the day by visiting some of the best places to see in Florence, including a monument, a palace, a church, a public square and much more! Start your adventure at Porta Romana. This increasingly popular monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Palazzo Salimbeni located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Basilica Of San Domenico. Its historic features will captivate you. After the church, continue your tour of the city with a visit to Siena Cathedral. Visitors usually appreciate the romantic features of this church. Next up is Pubblico Palace, a highly recommended palace. For a change of pace, head to Piazza Del Campo. As one of the most impressive attractions in Florence, this public square is the perfect place to end your self-guided sightseeing tour.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip in Italy!

Dive into day 11 of your remarkable road trip in Italy. Today you will explore Rome, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Rome. You’ll stay here for 3 nights.

Today’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Colosseum. This iconic archeological site is an UNESCO world heritage-listed place to see in Siena. Continue your discovery at Roman Forum, a picture-perfect archeological site with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Popolo. This top-rated public square offers a grand encounter with Siena. Next, make your way to Capitoline Museums to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

Continue your evening by exploring the vibrant nightlife scene at La Botticella Of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Almalu Trastevere, a bar that offers unique local touches. Likewise, Bar Viminale Di Pepi Maurilio provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day in Italy!

At the end of the day, you'll drive back to Rome, where you'll stay for 2 nights more.

A visit to Trastevere in Vatican City is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Vatican Museums is the perfect place to start. This art museum is one of the most iconic places to visit in Rome.

Nearby, you'll also find Campo De' Fiori and Piazza Navona. Visit these for an interesting touch to your journey.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

On day 13 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Today’s itinerary in Rome covers several incredible sights, including a church, a public square, a monument, a castle and much more! Start your adventure at Basilica Of San Clemente. This curiosity-inducing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Spanish Steps, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Piazza Di Spagna. This world-famous public square offers an enriching experience. For a change of pace, head to Trevi Fountain, where you can take in enchanting features. Conclude your self-guided sightseeing tour with a visit to Pantheon and Castel Sant'angelo. These sights offer a fulfilling end to a perfect day.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Continue your lively evening at The Apartment Bar Roma, a perfect place for winding down or revving up the night, depending on which mood you’re in. Hotel Hassler Roma is another excellent bar that offers a great selection of drinks to suit any mood.

Celebrate another amazing day of your road trip adventure in Italy!

On day 14 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Bologna. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Bologna Cathedral is the perfect place to start. This church is one of the most curiosity-inducing places to visit in Rome. Next, head to Piazza Maggiore, a spectacular public square, known for its culturally significant features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Two Towers. This breathtaking monument is a highly recommended experience. Nearby, you'll also find Porta Maggiore. Visit these for an interesting touch to your journey.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

After your meal, keep the night alive at a bar like Bhangrabar, known for its lively atmosphere. Rufus Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ostello Bello Grande offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!